Issue 44, 2022
From the journal:

Chemical Communications

Diastereodivergent synthesis of chromeno[2,3-b]chromenes by tuning all of the reactivity centers of isocyanoacetate†

Lei Wang,a   Zitong Huang,a   Xiaoyu Guo,a   Jian Liu,a   Jinhuan Dong*a  and  Xianxiu Xu*a  

* Corresponding authors

a College of Chemistry, Chemical Engineering and Materials Science, Collaborative Innovation Center of Functionalized Probes for Chemical Imaging in Universities of Shandong, Key Laboratory of Molecular and Nano Probes, Ministry of Education, Institute of Molecular and Nano Science, Shandong Normal University, Jinan, China
E-mail: dongjh@sdnu.edu.cn, xuxx677@sdnu.edu.cn

Abstract

A novel diastereodivergent tricyclization of isocyanoacetates with o-quinone methides was accomplished for the efficient synthesis of chromeno[2,3-b]chromene derivatives. All three reactive centers of isocyanoacetate reacted sequentially with two o-QMs, affording the products with four adjacent stereocenters in a diastereoselective manner. The asymmetric version was preliminarily investigated.

Graphical abstract: Diastereodivergent synthesis of chromeno[2,3-b]chromenes by tuning all of the reactivity centers of isocyanoacetate

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Article information

DOI
https://doi.org/10.1039/D2CC01632J
Article type
Communication
Submitted
22 Mar 2022
Accepted
04 May 2022
First published
04 May 2022

Chem. Commun., 2022,58, 6433-6436

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Diastereodivergent synthesis of chromeno[2,3-b]chromenes by tuning all of the reactivity centers of isocyanoacetate

L. Wang, Z. Huang, X. Guo, J. Liu, J. Dong and X. Xu, Chem. Commun., 2022, 58, 6433 DOI: 10.1039/D2CC01632J

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